Dichloromethane → 1-Undecene, 11,11-dimethoxy-

HRID 2118107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118107
[CH:1]([O-:6])([O-])[O:2][CH2:3]C.[CH:7](=O)[CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]C.Cl[CH2:20]Cl>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:20][O:6][CH:1]([O:2][CH3:3])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH2:7]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 624472-UndecenalHCID 53630039Ethylorthoformate

Produkt 1

HCID 1033751-Undecene, 11,11-dimethoxy-Ausbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

37.78 g of ethyl orthoformate (13.09 ml, 356 mmol, 2 eq.) and 1.691 g of para-toluenesulfonic acid (catalytic amount: 8.9 mmol, 0.051 eq.) are added to a solution of 30.05 g of 97% undecenal (37.10 ml, 173 mmol) dissolved in 500 ml of methanol. The reaction takes place over 12 hours and at reflux of the methanol. After addition of 500 ml of dichloromethane, the reaction mixture is washed successively with a 1% sodium carbonate solution (two times) and with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated to give 36.39 g of a brown liquid with a yield of 97%.

Aufarbeitung

  1. customover 12 hours
  2. washthe reaction mixture is washed successively with a 1% sodium carbonate solution (two times) and with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-358f32ced2c142e78352d1a7d0fda2ab
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442823B2

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